Jessie's Newest Maid
by Angels Sonata
Summary: [AU/One-Shot] Returning to Pallet Town after a long journey, Ash and Pikachu stop at a cafe to escape the rain. They encounter some familiar faces, but unknown to the pair that behind the scenes an old adversary has plans of her own and wants revenge for years of defeats and humiliation.


The rain fell heavily outside the small cafe that had been discovered on the road to Pallet Town. It wasn't something that Ash remembered being there, but he knew that a lot had changed on his travels. He had been on the road, returning home periodically for the past eight years and Ash knew that locations would always change with the times. Though he was quite thankful that the cafe was there. Had it not, he and Pikachu would have needed to find shelter in the forest. He still remembered the last time that had happened. It had been his first night into his journey as a Pokemon trainer.

The only thing that was missing was the thunder and lightning in the sky.

Smiling as he looked out of the window, Ash knew that it wouldn't be long and he and Pikachu would be home. He hadn't called ahead, the idea of surprising his mum, Professor Oak and Tracey would be worth it. Already he had visited Brock and Misty and now it was time to save the best to last.

Looking at the hot chocolate in his hands, Ash turned towards Pikachu and watched as the small mouse Pokemon ate into a dish of Pokemon food that had been provided by the cafe. Looking around, considering that it was chucking it down, Ash was amazed that apart from the two waitresses working and a Meowth lazing in the window, he was the only person there. Of course, how many people would be out in this weather? Ash and Pikachu had been caught out due to the fact that he looked at the weather reports and saw that it would be dry all day. That was the last time he would trust the weather reports.

"I guess it could be worse." Ash mused as he looked at the weather conditions outside, seeing the rain falling heavily. Pikachu perked up, looking at Ash before tilting it's head, letting out a small 'pika' to ask. "Oh, sorry Pikachu, just a lot on my mind. Remembering back to their escape from the flock of Spearow that had attacked them. Ash finished off his hot chocolate before taking out his pokedex, checking the time and wondering whether or not the rain was going to let off. If it wasn't, then the option of going the rest of the way on foot wasn't particularly appealing. "Enjoying that, Pikachu?" Ash asked, gesturing to the food.

"Pika, pika pika-chu." The Pokemon responded before Ash chuckled and put his mug to the side. As he did, one of the waitresses, a tall lady, slender of body with a cute white and pink maid's dress with frilled petticoats and a skirt that reached just above her knees. Mahogany brown hair reached down to the small of her back and she smiled warmly, her face perfectly made up and her dark eyes looked on at Ash. To the young man sitting before her, there was an air of familiarity. Like the two of them had met on their travels, yet Ash couldn't recall.

"Can I get you another hot chocolate?" the maid asked with a smile on her face and a soft voice as she took the empty mug away from the table. "Perhaps something to eat?"

"I'll have another hot chocolate. Also, do you have a phone I can use?" Ash asked, and the maid giggled before pointing to the door just past the counter. "Thank you. I won't be a moment Pikachu." Ash finished before getting up from the table, and walking to the indicated area.

-X-

Watching through the cameras that were set up on the walls of the café, the feed coming live in the control room of the building; a crimson haired woman watched in earnest as the young man got up from the table and left the Pikachu where it was.

After a year of planning it was finally happening. With a slight cackle, the woman sat back and continued to watch. She picked up a mug with a large red R on it, sipping the drink and smiling to herself.

"I wanted to inform you Mistress, that everything is running smoothly. Gabrielle has done what you asked." Standing at the doorway into the control room, another maid stood waiting patiently. The red haired woman turned to face the blue haired maid and grinned at what she had just been told. Like her counterpart in the main area of the cafe, the maid was dressed in a frilly maid's dress that matched her hair colour. White frills decorated both the skirt's hemline and the puffy sleeves covering her elbows. Apart from the bodice, which was covered with lace and bows, the dress was otherwise plain and unadorned "What shall we do now?"

The woman didn't answer at first. She turned to the maid before getting up, walking over and kissing the girl on the cheek. "We wait, my dear Jasmine. Go and fetch me a hot drink my dear Jasmine. For the moment, it's just a matter of waiting for the spiked drink and food to take effect and then the twerp and his rat will be out for the count." she ordered before stepping back and brushing off her black dress and turning back towards the monitors, watching the young man's Pikachu with an evil grin across her face.

The plan that she was concocting had been a long time coming. Setback after setback had delayed her but with the help of items that had once belonged to the Team Rocket organisation, she was in place for the last part of the plan. Now she was so close, so close to pulling it off and she would finally have what she wanted. Payback.

Though he may have aged and time had passed, the old saying was that revenge was a dish best served cold. This revenge was a long time coming, and the wrongs of the past would be made right.

-X-

Ash stared at the phone. He had tried to call through to Professor Oak and his mum repeatedly, each attempt ending with the same message saying that the call couldn't get through. Perhaps it was the weather. He glanced out the nearest window and the rain was falling quite heavily. Maybe that was the reason. It was the only one that made sense. Ash hoped that it was something as innocent as that, but only time would tell. He was a few hour's walk from Pallet Town. He'd be home soon and Ash would see that there was nothing to worry about.

Putting the phone on the receiver, Ash stepped out into the seating area, covering his mouth and yawning as he walked back to the table. He looked towards Pikachu, the mouse Pokemon had fallen asleep at the table, resting up against the dish of food.

'Looks like we both could do with a sleep.' Ash thought as he gathered up his backpack and possessions. He looked around, still amazed that it was raining heavily out there. He really should let the weather ease up first, but time was of the essence and he couldn't delay. Ash wanted to return home as quick as possible. To see Professor Oak, his Pokemon, to see his mother. Reaching down to pick Pikachu up from the table, Ash yawned again, this time unable to cover his mouth.

"How sweet, the young trainer is getting tired." Even in his current state, Ash was aware of his surroundings. The voice... it was too familiar. It belonged to a woman that had been a constant thorn in his side and his companions. Her, and the organisation she had worked for. Turning around, trying to keep himself awake, Ash looked upon the woman. Her long red hair all too familiar. Ash shook his head and reached around for one of his Pokeballs.

"Jessie... what... what are you doing?" Ash asked, his eyes were getting heavy, he was about to fall asleep in the worse possible situation. "What did you do to Pikachu?"

Jessie didn't answer at first. She simply laughed and stepped closer towards the boy, a grin creasing her features. "I didn't do anything. Your poor Pokemon is simply sleeping. He's tired, just like you are." Jessie answered and before Ash could say anything, he slumped to the ground. He had tried to keep himself awake but nothing worked. In the end, the Pokeball he grasped in his hand rolled to the floor, away from Ash's sleeping body.

-X-

Ash's sleeping form, as well as that of Pikachu's, was moved from the cafe to a mansion not too far from where Pallet Town was located. It was surrounded by a brick-wall fence that kept out inquisitive eyes. An electric fence controlled who came in and who came out. The gardens were kept green by groups of landscapers and gardeners. Cleaners kept the outside windows spotless. Maids patrolled the interior of the mansion and ensured that all looked was neat and tidy. After all, Jessie had enforced her rules strictly. Nothing but perfection would satisfy the crimson haired mistress of the mansion.

Locked within a single room, bound to what resembled a salon chair, Ash was bound to the arm-rests with tight rope, metal clasps held his feet down and apart from a pair of white panties, Ash's clothing had been removed and disposed of. The young man slowly came to, eyes opening slowly and Ash groaned as he came to look upon his surroundings. Bare walls, no windows, a number of chests and a wardrobe to both sides along with a single door right in front of Ash, almost as a way of teasing him, tormenting him with the knowledge that were it not for the bindings holding him to the chair, he could escape. Assuming it was locked of course.

"Where... where am I?" Ash asked himself, wanting to rub his eyes but growing frustrated with the fact that he couldn't move his arms or legs. Thinking back, he remembered what had happened. The cafe, the telephone not working, Jessie. "Great, what is she up to now?"

When the question came out of Ash's lips, the woman herself stepped through the door. Gone was the black business like dress she had worn, in its place was a more luxurious gown of dark green velvet that wrapped around her body like a second skin, flowing around her legs, ending in a train that spread across the floor behind her. Her red hair was elegantly styled. Before Jessie's hair would flow behind her, now it was styled in an up-do that was held in place with a number of pins. She had seemingly heard Ash's comment and couldn't help but chuckle at the question. She shook her head and stepped forward.

Ash had to admit that out of her Team Rocket uniform, she was quite attractive.

"What I'm up to, my dear boy, is quite simple. Its a matter of revenge."

"By knocking me out, stripping me down to my underwear and strapping me to this chair? Not exactly normal." Ash responded, smirking at the fact that, minus being stripped to his underwear, this wasn't exactly original. "Where's Pikachu?" Jessie raised an eyebrow before clicking a finger. A maid stepped through, though it was the same mahogany haired maid from the cafe, still wearing her white and pink outfit. She was wheeling a tray inside. On the top was a glass case with Pikachu trapped inside. It immediately cried out, before producing an electric shock that did nothing but charge the battery that was hooked up to the box through a number of cables and wires that fed through the glass and onto pads that had been placed upon Pikachu's red cheeks. Jessie looked on at the display, merely chuckling at the futile attempt to try and break free of the box. She shook her head before turning back to the bound and captive Ash who looked on at horror at the treatment of his oldest friend and partner.

"Spirited, I'll give him that. He certainly takes after his trainer."

"Let him go!" Ash shouted as he watched while Pikachu slowly drained himself of energy. "You have me bound up, what more could you want Pikachu for?"

"Oh we'd let him go. Happily for that matter. You see, I'm no longer in Team Rocket and so Pokemon hold no real interest for me. I'd let Pikachu go, but he'd run to get help and bring them back here which would bring my entire operation crashing to the ground." While Jessie explained everything, she waved her arms around in the air in a dramatic display. "Which is why I have come up with an idea!" the woman took out a Pokeball, releasing a new Pokemon out in front of them. Gothorita rose up and looked around before turning to Jessie, performing a curtsey before awaiting a command. "Gothorita my dear, hypnotise Pikachu and calm him down." The Pokemon let out a small sound of obeisance and leapt up onto the train. It began to concentrate, performing its special move before waving its arms around, putting the mouse Pokemon into a trance, causing Pikachu to stop shocking the case before it simply let out a sigh of contentment and pleasure.

With Pikachu calm enough, the maid opened the top seals and picked him up, placing him in front of the box so that Ash could see how tranquil his partner now appeared.

Without another word, the restraints that held Ash down were released. He got up and made to rush over to Pikachu but an unspoken command from Jessie to Gothorita caused the Pokemon to turn on Ash, its eyes glowing a pale blue. Ash was immobilised temporarily. "What..." Ash found himself struggling to control his own body. Jessie had a pokeball in the palm of her hand and without his command, Ash's body moved so that he was picking it up. He took the pokeball, turned to Pikachu, and said the words that he had never believed he would say:

"Pikachu, return."

There was a red beam shooting out from the Pokeball, it hit Pikachu square on and in its calm state, the mouse Pokemon didn't even to try and resist. It returned to the Pokeball and didn't struggle to break free.

Ash could only stare in horror at what had just happened. His best friend returning to its Pokeball, and Ash doing it. He realised that Gothorita was controlling his movements and the Pokemon forced Ash to hand the ball containing Pikachu to his best friend before he was made to sit on the chair. Only this time the restraints didn't engage and trap him. The Pokemon was doing that job for Jessie.

"Now that you've seen a demonstration of what Gothorita can do, I think its time I give you the basics of what is happening." Jessie explained everything. That when Team Rocket disbanded she made her own way in life, only bringing along James and Meowth until they served their purpose. She had managed to accumulate funds from her time with the international organisation, gathering enough money so she could start over with the mansion that they now occupied. Of course that hadn't been the end. Far from it. One of Team Rocket's final experiments was with psychic Pokemon that could be used to create obedient members of the organisation. With multiple hypnosis sessions, the effects were near enough permanent.

That was where James came in. Jessie clicked her fingers again and summoned another maid. This one had blue hair and a blue maids uniform. She stood with a smile, again she was familiar to Ash, but he couldn't recall where from. That was until Jessie filled in the blanks. "I don't know how perceptive you are, in the past you never did see through our disguises. But I'd like you to meet Jasmine, my chief-maid. You formally knew her as James." Ash realised what had happened at that point, amazed beyond belief. Had he not been told, he would have thought that the maid had been born a girl.

"So if that's..."

"Ah you're catching on quickly. Meet Gabrielle, or your longest rival." It was Gary. Hypnotised and feminised into a sissy maid. Ash knew what was coming next. It was the only thing that made sense. The maid that was Gary left the room, only to return later with box that was placed next to Gothorita. Jessie took the lid off the box, revealing a brand new maid's outfit. This one was pink, frilled along the hemline of the knee-length skirt. Puffed sleeves would cover the shoulders and lacing on the back was as soft as silk. Petticoats were taken out next, then stockings and finally a pair of heeled shoes. There were other items that had been brought in, amongst them was a blonde wig with multiple curls. Also included was a bra, corset and panties. From the amount of times that Ash had been dressed up, he definitely knew what was coming.

"Gothorita, if you please." Jessie requested, and the psychic Pokemon pulled Ash from the chair so that he was standing on his own two feet.

Gabrielle and Jasmine took up an item each. Gabrielle stepped in first, replacing the white panties Ash was wearing with a pair of frilled pink panties that, with a bit of positioning of his genitals, created the image of a flat groin. Jasmine stepped in afterwards, a corset, pink and white, in her hands and was unlaced and ready to be slipped around Ash's chest. The metal clasps were pulled together before the maid stepped behind Ash, taking the lacing of the garment and with all the strength she could muster, pulled the corset in tightly, reducing the size of Ash's waistline and shaping his body. Ash grunted in pain, unable to move or fight back thanks to the power of Gothorita's psychic abilities. He let out a few wheezing breaths, far from used to the pressure being applied to his body.

Jessie meanwhile watched as her two maids prepared the newest member of staff. "You know, this reminds me of the first time we dressed you up so you could sneak into Erika's gym. I wonder what she is up to." the older woman mused with a small grin on her face before shaking off the thought, going back to watching the sight of Ash unfold as Gabrielle prepared a bra that matched the underwear, only this one had a pair of breast forms that were a C-cup in size. They were pressed to Ash's chest above the corset and the bra itself clipped in place. He was shaping up quite nicely in Jessie's eyes.

It didn't take long, but Ash was fully dressed up and looking like the maid Jessie wanted him to be. He was standing stock still, the blonde wig on top of his head and covering all traces of his original black hair. The young man was shivering, shaking and nervous at how he appeared. Jessie had tasked that Jasmine and Gabrielle make the young man over, something they relished doing. No longer looking like the Pokemon trainer he had been, Ash looked like a maid.

Yet Jessie wasn't done yet.

"A wonderful job my sissies, a wonderful job indeed. You've turned Ash into a wonderful maid. Dare I see, he no longer deserves to be called Ash. I think Ashley is a much better name."

"Thank you Mistress Jessie." The two maids said in unison before dipping in a curtsey at the compliments received before Jessie turned to Gothorita. "One last task my dear Gothorita."

"Please... Jessie don't do this. This isn't right!" Ash called out, shaking his head and causing the blonde curls to flick around him as he did so. It almost looked as if he were about to cry, something that wouldn't bother Jessie. His make-up was waterproof after all and required the best facial cleansing products on the market to remove.

Ash's pleas fell on deaf ears as Jessie turned towards Gothorita and gave her another command. "Hypnosis." The immobilisation power that Gothorita was using on Ash soon gave away to hypnosis. Ash tried not to look at the Pokemon, but it was too late. Ash was under the sway of Gothorita, and by proxy, under Jessie's command at the same time. The woman simply grinned and took advantage of the moment.

"Everything you do from here, you do for the good of your mistress." Jessie spoke, her words echoing through Ash's mind, coercing him and causing him to take everything that she said as the truth and slowly nodded his obedience. "Your name is Ashley, you are a maid in my service. You are no longer devoted to Pokemon training or travelling across the lands. You shall remain in the mansion serving me, cleaning the building and aiding your sisters in your chores and their chores. There is nothing you would not do for me, no where you will not go. Whatever I tell you to do, you shall obey."

"Yes Mistress Jessie. I am Ashley, your maid. I shall work for you and serve you in any way possible. No matter what is asked of me." Ash repeated the words, and with a click of her fingers, Jessie ended Gothorita's hypnosis attack, the Pokemon slumping to the base of the tray before Jessie returned her to the pokeball. She turned towards Ash, wondering whether or not the hypnosis had worked.

"Ashley, how do you feel?" Jessie asked.

"I... I feel fine, thank you for asking Mistress. How may I be of service to you?" Although the voice that was speaking was Ash's original male voice, his thoughts were of a girl, a maid who's only duty was to the mistress of the mansion. Jessie grinned at this, knowing that she had Ash, or Ashley, under her control from that point on.

As it was late, there was no choice but to dismiss the maids and allow them to enjoy the evening. "Gabrielle, Jasmine, take our newest maid to the quarters and make sure she is made to feel... welcomed, by the other girls."

"Of course mistress." The other two maids said in unison before leaving with Ashley from the room, shutting the door behind them.

Ashley was taken to a room on the top floor and down the corridor on the east wing of the building. When Gabrielle opened the door for them, Ashley came across numerous maids that were in various states of dress. Some still wore their maid uniforms, others wore next to no clothes other than bras and panties that showed off distinctive bulges in their groin areas. These were the other victims of Jessie's hypnosis and her plans to live in luxury.

Jasmine stepped forward, a smile upon her face as she called the others to attention. "Girls, this is Ashley. She's just joined us!" The maid began in an upbeat tone of voice. "We've been tasked with making her feel welcome, so you know what that means!" At that, the maids let out squeals of approval before moving to introduce themselves to the newest maid and make her feel welcome in the mansion.

Ashley on the other hand simply accepted it as her new life. The hypnosis was complete in his mind. His old life was gone, and his new life was ahead of him. How long it lasted was anyone's guess, but if Jessie had anything to do with it, then Ashley would be under her thumb for quite a while.


End file.
